Let me go through this beyond just Novak and Rafa, because it's an interesting one to consider.
2003 Wimbledon -- This is a tough one... I think Big Mark would like his chances against Andy. I think Philippoussis might have been Wimbledon champ.
Mark Philippoussis - 1W
2004 Australian Open -- Tough to look past Marat here. I know he played a bunch of 5 setters, so tiredness is maybe a factor, but he knocked off 2 slam holders in succession. I don't think anyone got close enough to Federer on the other side to make me think they'd have a shot against him.
Mark Philippoussis - 1W
Marat Safin - 2AO, 1 USO
2004 Wimbledon -- I think Roddick is unstoppable here. I know Lleyton will have liked his chances, but if Roddick played Federer as close as he did I can't see Hewitt stopping him.
Mark Philippoussis - 1W
Marat Safin - 2AO, 1 USO
Andy Roddick - 1USO, 1W
2004 US Open -- I think it probably comes down to Hewitt and Agassi. Is Andre's case inflated on account of how much wind there was on QF day? I don't know, but Hewitt was so very, very far away on finals day I'm really tempted to think Agassi could have outlasted him.
Mark Philippoussis - 1W
Marat Safin - 2AO, 1 USO
Andy Roddick - 1USO, 1W
Andre Agassi - 4AO, 1RG, 1W, 3USO
2005 Wimbledon -- Now this is a tough one. I'm pretty sure it was this year that Hewitt was pissed he was in Roger's half instead of Andy's, and given Roddick's Saturday semi finaling I am tempted to think he might have had a case.
Mark Philippoussis -- 1W
Marat Safin - 2AO, 1 USO
Andy Roddick - 1USO, 1W
Andre Agassi - 4AO, 1RG, 1W, 3USO
Lleyton Hewitt - 2W, 1USO
2005 US Open -- It's tough to pick against Agassi here, and for 3 sets in that final his effort was so high that especially with that crowd behind him you have to like his chances of beating almost anyone, but Hewitt always thrived in hostile environments in a way Federer never really did, and given Andre's back to back 5 setters you have to believe he was there to be ground down. Too close to call, but I'll go with the head over the heart, and say Hewitt gets his revenge after losing the potential final the year before
Mark Philippoussis - 1W
Marat Safin - 2AO, 1 USO
Andy Roddick - 1USO, 1W
Andre Agassi - 4AO, 1RG, 1W, 3USO
Lleyton Hewitt - 2W, 2USO
2006 Australian Open -- Wide open. I think cases can be made for Haas, Davydenko, Kiefer, and Baghdatis. It's hard to pick against Baghsy, especially with the crowd support that he was getting, but all of those 5 setters had to have caught up to him eventually. I feel like Davydenko would almost certainly have choked in that atmosphere, but Kiefer, and certainly Haas? I think the closeness of those first 2 sets in the final make me think Baghdatis has a decent shot against those lesser dudes.
Mark Philippoussis - 1W
Marat Safin - 2AO, 1 USO
Andy Roddick - 1USO, 1W
Andre Agassi - 4AO, 1RG, 1W, 3USO
Lleyton Hewitt - 2W, 2USO
Marcos Baghdatis - 1AO
2006 Wimbledon -- Don't really see anyone else toppling Nadal, though I think Ancic would probably have been the guy across the net.
Mark Philippoussis - 1W
Marat Safin - 2AO, 1 USO
Andy Roddick - 1USO, 1W
Andre Agassi - 4AO, 1RG, 1W, 3USO
Lleyton Hewitt - 2W, 2USO
Marcos Baghdatis - 1AO
Rafael Nadal - 1AO, 10RG, 3W, 2USO
2006 US Open -- I think Roddick is probably the guy here. Though I think Blake would probably be the guy in his way, and I don't think he would go away easy. That QF with Fed was one of my faves from 2006.
Mark Philippoussis - 1W
Marat Safin - 2AO, 1 USO
Andy Roddick - 2USO, 1W
Andre Agassi - 4AO, 1RG, 1W, 3USO
Lleyton Hewitt - 2W, 2USO
Marcos Baghdatis - 1AO
Rafael Nadal - 1AO, 10RG, 3W, 2USO
2007 Australian Open -- I like Roddick's chances here. He might have been schooled in that semi final, but you've always got to like his chances against Gonzo, and especially if we're thinking he's coming off a USO win he'd be high on confidence.
Mark Philippoussis - 1W
Marat Safin - 2AO, 1 USO
Andy Roddick - 1AO, 1W, 2USO
Andre Agassi - 4AO, 1RG, 1W, 3USO
Lleyton Hewitt - 2W, 2USO
Marcos Baghdatis - 1AO
Rafael Nadal - 1AO, 10RG, 3W, 2USO
2007 Wimbledon -- Less reason to doubt than in 2006. Nadal with ease.
Mark Philippoussis - 1W
Marat Safin - 2AO, 1 USO
Andy Roddick - 1AO, 1W, 2USO
Andre Agassi - 4AO, 1RG, 1W, 3USO
Lleyton Hewitt - 2W, 2USO
Marcos Baghdatis - 1AO
Rafael Nadal - 1AO, 10RG, 4W, 2USO
2007 US Open -- This is a good one. I think the final is Roddick and Djokovic. Both of them fought Roger very close for 2 sets, while Novak remained closer in the third than Andy did, and Novak had beaten Andy in Canada a few weeks prior, but in this fantasy scenario where Roddick is defending champ, and given how he was more often than not a bad match up for Novak I'd give it to him.
Mark Philippoussis - 1W
Marat Safin - 2AO, 1 USO
Andy Roddick - 1AO, 1W, 3USO
Andre Agassi - 4AO, 1RG, 1W, 3USO
Lleyton Hewitt - 2W, 2USO
Marcos Baghdatis - 1AO
Rafael Nadal - 1AO, 10RG, 4W, 2USO
2008 US Open -- Djokovic. Obviously.
Mark Philippoussis - 1W
Marat Safin - 2AO, 1 USO
Andy Roddick - 1AO, 1W, 3USO
Andre Agassi - 4AO, 1RG, 1W, 3USO
Lleyton Hewitt - 2W, 2USO
Marcos Baghdatis - 1AO
Rafael Nadal - 1AO, 10RG, 4W, 2USO
Novak Djokovic - 6AO, 1RG, 3W, 3USO
2009 Roland Garros - Another good one. I think Delpo and Soderling is the final, and one of these men is a proven final choker, while one is a proven riser to the occasion. Maybe there is less chance of Soderling choking if he's facing a baby instead of a legend, but I still think Delpo outhits him, and against a player like Soderling is less likely to be concerned by the physical troubles he had going the distance with Federer.
Mark Philippoussis - 1W
Marat Safin - 2AO, 1 USO
Andy Roddick - 1AO, 1W, 3USO
Andre Agassi - 4AO, 1RG, 1W, 3USO
Lleyton Hewitt - 2W, 2USO
Marcos Baghdatis - 1AO
Rafael Nadal - 1AO, 10RG, 4W, 2USO
Novak Djokovic - 6AO, 1RG, 3W, 3USO
Juan Martin Del Potro - 1RG, 1USO
2009 Wimbledon -- Yeah, nobody else in that draw is stopping Roddick here.
Mark Philippoussis - 1W
Marat Safin - 2AO, 1 USO
Andy Roddick - 1AO, 2W, 3USO
Andre Agassi - 4AO, 1RG, 1W, 3USO
Lleyton Hewitt - 2W, 2USO
Marcos Baghdatis - 1AO
Rafael Nadal - 1AO, 10RG, 4W, 2USO
Novak Djokovic - 6AO, 1RG, 3W, 3USO
Juan Martin Del Potro - 1RG, 1USO
2010 Australian Open -- Can't see past Muzza here.
Mark Philippoussis - 1W
Marat Safin - 2AO, 1 USO
Andy Roddick - 1AO, 2W, 3USO
Andre Agassi - 4AO, 1RG, 1W, 3USO
Lleyton Hewitt - 2W, 2USO
Marcos Baghdatis - 1AO
Rafael Nadal - 1AO, 10RG, 4W, 2USO
Novak Djokovic - 6AO, 1RG, 3W, 3USO
Juan Martin Del Potro - 1RG, 1USO
Andy Murray - 1AO, 2W
2011 Roland Garros -- Maybe the most obvious one out of all of them?
Mark Philippoussis - 1W
Marat Safin - 2AO, 1 USO
Andy Roddick - 1AO, 2W, 3USO
Andre Agassi - 4AO, 1RG, 1W, 3USO
Lleyton Hewitt - 2W, 2USO
Marcos Baghdatis - 1AO
Rafael Nadal - 1AO, 9RG, 4W, 2USO
Novak Djokovic - 6AO, 2RG, 3W, 3USO
Juan Martin Del Potro - 1RG, 1USO
Andy Murray - 1AO, 2W
2012 Wimbledon - Wouldn't pick against Andy here. I think he was really good in that final, and Novak pretty lacklustre through most of 2012.
Mark Philippoussis - 1W
Marat Safin - 2AO, 1 USO
Andy Roddick - 1AO, 2W, 3USO
Andre Agassi - 4AO, 1RG, 1W, 3USO
Lleyton Hewitt - 2W, 2USO
Marcos Baghdatis - 1AO
Rafael Nadal - 1AO, 9RG, 4W, 2USO
Novak Djokovic - 6AO, 2RG, 3W, 3USO
Juan Martin Del Potro - 1RG, 1USO
Andy Murray - 1AO, 3W
I don't think anything actually changes here, but I think Stan makes the final at Wimbledon in 2014, and given how well he was playing till half way through that second set against Fed, and given how poor Novak looked through both his last 2 matches... There might have been something there...
I think Murray would put up a hell of a fight in the 2015 final too.
USO 2015... Final against Stan? Hmm... Who knows. Still think Novak comes through considering how much he actually overcame that night, but all three of those finals might have been really interesting.
I think Cilic might have made the 2016 Wimbledon final, and though he's likely to have choked... Maybe... Not?
2017 Australian Open - Nadal
Mark Philippoussis - 1W
Marat Safin - 2AO, 1 USO
Andy Roddick - 1AO, 2W, 3USO
Andre Agassi - 4AO, 1RG, 1W, 3USO
Lleyton Hewitt - 2W, 2USO
Marcos Baghdatis - 1AO
Rafael Nadal - 2AO, 9RG, 4W, 2USO
Novak Djokovic - 6AO, 2RG, 3W, 3USO
Juan Martin Del Potro - 1RG, 1USO
Andy Murray - 1AO, 3W
2017 Wimbledon - Yeesh... Berdych? Dimitrov? If we consider Cilic did in fact pick up his blister issue in the semi final then I can't see any way that he wins this. I think it would have been Grigor and Berdy in the other semi final, and... Well, it'd be one of them.
Here's the other question... What happens at Wimbledon 2001??? I like Rafter's chances.
Mark Philippoussis - 1W - 1
Marat Safin - 2AO, 1USO - 3
Andy Roddick - 1AO, 2W, 3USO - 6
Andre Agassi - 4AO, 1RG, 1W, 3USO - 9
Lleyton Hewitt - 2W, 2USO - 4
Marcos Baghdatis - 1AO - 1
Rafael Nadal - 2AO, 9RG, 4W, 2USO - 17
Novak Djokovic - 6AO, 2RG, 3W, 3USO - 14
Juan Martin Del Potro - 1RG, 1USO - 2
Sir Andy Murray - 1AO, 3W, 1USO - 5
Grigor Dimitrov - 1W - 1
Pat Rafter - 1W, 2USO - 3